Almost every founder I coach has one person they can't quite figure out.
It rarely comes up first. We work through the product, the pipeline, the new hire, wins, blockers, etc. Then, near the end, almost as an afterthought, it surfaces: "I just have this one person on the team..."
And here's the strange part. They defend the person in the same breath they complain about them. They're smart. They're loyal. They've been here for years. They do this one thing better than anyone. The work gets done.
But the founder is worn out by them. The team braces when they walk into a meeting. Feedback bounces off. Every exchange carries a little edge, a jab you can feel but can't quite name. And the founder feels guilty even raising it, because what's the actual complaint? "They do their job"?
That's the trap of the how. When someone does the right things the wrong way, there's nothing clean to point at, so you say nothing, and it quietly leaks into everything.
THE BIG INSIGHT
The way work gets done is part of the work. If the result shows up with damage attached, the job isn't as finished as it looks. You manage what you measure, and most leaders only measure the what. So you tell yourself the person is fine, because you can point to what they produced, while the team pays for how they produced it.
The Same Problem Wears Three Faces
When someone does the right things the wrong way, it usually shows up as one of three patterns. The person you just pictured is probably one of them.
Results at everyone else's expense. They hit the goal, but they leave a wake. Peers get steamrolled, and the team burns energy recovering from how the win happened. The scoreboard says they're winning. The people around them are losing.
The task without the ownership. You ask for one thing and you get exactly that, nothing more. No judgment, no flag when something looks off, no "I noticed this while I was in there." Technically they did what you said. That's the whole problem. You wanted someone who thinks. You got someone who complies, and now you do the thinking for both of you.
Competent but corrosive. They're genuinely good at the work, and also defensive about feedback, dismissive of peers, or territorial. The skill is real, which is what makes it dangerous, because it buys cover. Nobody wants to challenge the person who delivers, so the behavior compounds and the culture reorganizes itself around tolerating it. The little digs and zingers feel minor. They're not. They wear a team down, because there's nothing to build on, just a slow drip that teaches everyone to keep their guard up.
Different on the surface, same root underneath. In all three, the result gives the person cover, and everyone else absorbs what it cost.
How to Manage the How Without Losing the Person
People don't remember what you know. They remember how they felt working with you. For most roles, the how isn't a soft extra. It's the job. Here's how to get it back on the table without blowing up the person.
Make the cost visible, to yourself first. Add up the hours you spend managing around this one person, the meetings you replay, the energy you lose, the strong team you can't quite build. That's the tax. You've just never put it on the books.
Raise it with the whole team, not in an ambush. The instinct is to pull the person into a one on one and unload. Don't. That feels like an attack before you start. Name it to everyone: "I've been clear about what we get done and silent about how. I want us to start talking about both, and I want you to hold me to it." Now it's a standard, not a verdict on one person.
Define the how as concretely as the what. "Be better" is not a standard. The what is the task; the how is the way it gets done: on time, in a way that builds trust and makes teammates stronger instead of smaller. Make it specific. "Handle the client issue" becomes "handle it, and keep the team looped so nobody gets blindsided." Name the behaviors the role needs the same way you'd name the deliverables.
Have the honest conversation, and keep steering back. Here's the hard part. You raise the how, they answer with the what. You press on the how, they point at someone else. That deflection is the problem itself. Stay calm and keep bringing it back to the one thing they control, which is how they operate.
Name the bar, and a timeline. Decide what "good" looks like in plain behavior, and by when you expect to see it. A how problem with no bar becomes something you tolerate for years. A how problem with a clear bar becomes coachable, or it becomes a decision you can finally make.
Through all of it, keep it about how they work, not who they are. Sometimes, once it's on the table, you both see the fit isn't there. That's not a failure. It's clarity you can act on.
QUESTIONS
Q: What if I'm friends with the person?
That friendship is probably why it's gone this long. You've extended grace you'd never give a stranger, and the digs land softer coming from a friend. But friendship doesn't lower the bar, it raises what you owe them: the truth. Say both parts out loud. "I'm telling you this because we're friends, and because I'm also your boss, and I haven't been fair to either of us by letting it slide." The kindest thing you can do for a friend is be the one person willing to say what everyone else only says behind their back.
Q: Someone on my team didn't used to be like this. Now it's bad. What changed?
People rarely curdle for no reason. Usually the role changed and they didn't, or they did and the role didn't. Someone who used to have authority and lost it, someone the company outgrew, someone who feels passed over and never said so. The new behavior is usually old resentment finally leaking out. So don't just manage the behavior, get curious about the shift. What changed for them, and when? You'll often find the how went sour the moment they stopped feeling seen, and that's a conversation you can actually have.
Q: How often does coaching actually turn someone like this around?
Honestly, less often than you'd hope and slower than you'd like. I've seen it take a year with plenty of backsliding, and I've seen it never take at all. Here's the tell, and you'll spot it in the first couple of conversations.
Can they say "you're right, that's on me," even once? Improvement tracks self-awareness and willingness to be coached, not talent. The ones who can own a sliver of it grow. The ones who only ever explain why it's everyone else rarely move, no matter how good the coaching.
Here's a gut check that cuts through all of it. Picture that one person and ask: knowing everything I know now, would I hire them again for the role they're actually in? If it's a quick yes, go invest in their how. If you hesitated, that hesitation is information, and it's worth getting honest about now instead of two more exhausted years from now.
Chad Todd
chadtodd.com
P.S. If you've got a name in mind, you don't have to figure out the conversation alone. Reply and tell me about them, and I'll help you find the first move.